DORIPENEM

Search structure
Trade Names:
Synonyms:
Status: Approved (2007)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: J01DH04
UNII: BHV525JOBH

Structure
InChI Key AVAACINZEOAHHE-VFZPANTDSA-N
Smile C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](CNS(N)(=O)=O)C3)[C@H](C)[C@H]12
InChI
InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H24N4O6S2
Molecular Weight 420.51
AlogP -1.6
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 7.0
Polar Surface Area 162.06
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 27.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial penicillin-binding protein inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
- - - - 0
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 1995 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Urinary Tract Infections 4 D014552 ClinicalTrials
Bacterial Infections 4 D001424 ClinicalTrials
Pancreatitis 3 D010195 ClinicalTrials
Cholecystitis 3 D002764 ClinicalTrials
Pneumonia, Ventilator-Associated 3 D053717 ClinicalTrials
Peritonitis 3 D010538 ClinicalTrials
Appendicitis 3 D001064 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Meningitis 1 D008581 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 16.0
Nervous system disorders Headache 15.0
Gastrointestinal disorders Diarrhoea 14.0
Gastrointestinal disorders Diarrhoea 12.0
Gastrointestinal disorders Nausea 12.0
Gastrointestinal disorders Diarrhoea 11.0
Blood and lymphatic system disorders Anaemia 10.0
Gastrointestinal disorders Diarrhoea 10.0
Nervous system disorders Headache 10.0
Gastrointestinal disorders Diarrhoea 9.0
Gastrointestinal disorders Nausea 9.0
Gastrointestinal disorders Nausea 8.0
Vascular disorders Phlebitis 8.0
Gastrointestinal disorders Nausea 7.0
Blood and lymphatic system disorders Anaemia 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Diarrhoea 6.0
Gastrointestinal disorders Nausea 6.0
Vascular disorders Phlebitis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Blood and lymphatic system disorders Anaemia 5.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Nervous system disorders Headache 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Nervous system disorders Headache 4.0
Gastrointestinal disorders Nausea 4.0
Vascular disorders Phlebitis 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Infections and infestations Candida infection 3.0
Nervous system disorders Headache 3.0
Gastrointestinal disorders Oral candidiasis 3.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Blood and lymphatic system disorders Anaemia 2.0
Infections and infestations Candida infection 2.0
Gastrointestinal disorders Colitis 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Infections and infestations Infection 2.0
Gastrointestinal disorders Oral candidiasis 2.0
Vascular disorders Phlebitis 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Blood and lymphatic system disorders Anaemia 1.0
Infections and infestations Candida infection 1.0
Gastrointestinal disorders Colitis 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Infections and infestations Infection 1.0
Gastrointestinal disorders Oral candidiasis 1.0
Vascular disorders Phlebitis 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Skin and subcutaneous tissue disorders Dermatitis 0.2
Investigations Hepatic enzyme increased 0.2
Skin and subcutaneous tissue disorders Rash 0.2
Gastrointestinal disorders Diarrhoea 0.1
Infections and infestations Infection 0.1
Gastrointestinal disorders Nausea 0.1
Skin and subcutaneous tissue disorders Pruritus 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Infections and infestations
10.98
Investigations
10.47
Hepatobiliary disorders
8.61
Gastrointestinal disorders
7.43
General disorders and administration site conditions
6.93
Injury, poisoning and procedural complications
6.59
Respiratory, thoracic and mediastinal disorders
6.25
Vascular disorders
5.91
Blood and lymphatic system disorders
5.74
Skin and subcutaneous tissue disorders
5.24
Immune system disorders
4.56
Renal and urinary disorders
4.56
Nervous system disorders
3.38
Metabolism and nutrition disorders
2.53

Cross References

Resources Reference
ChEBI 135928
ChEMBL CHEMBL491571
DrugBank DB06211
DrugCentral 4149
EPA CompTox DTXSID2046678
FDA SRS BHV525JOBH
Human Metabolome Database HMDB0041883
PDB O6P
PubChem 73303
SureChEMBL SCHEMBL37471
ZINC ZINC000003922770
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